3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol

Base Information

• Chemical Name: 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol
• CAS No.: 115890-33-0
• Molecular Formula: C₁₄H₁₉N₃O₃
• Molecular Weight: 277.323
• Mol file: 115890-33-0.mol

Synonyms:3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol

Chemical Property of 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol

There total 5 articles about 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Toluene-4-sulfonic acid (S)-2-benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (170936-50-2) → 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol (115890-33-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 - 80 ℃; for 12h;

Reference yield: 85.0%

3-azido-1,2-O-isopropylidene-3-deoxy-D-erythritol (1010701-88-8) + benzyl bromide (100-39-0) → 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol (115890-33-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 3h;

DOI:10.1021/jo800934b

Reference yield:

(2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol (91274-05-4) → 3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol (115890-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) (Bu)2SnO / 1.) MeOH, reflux, 5 h, 2.) DMF, 80-80 deg C

2: 95 percent / pyridine / 12 h / 0 °C

3: 90 percent / NaN₃ / dimethylformamide / 12 h / 70 - 80 °C

With sodium azide; di(n-butyl)tin oxide; In pyridine; N,N-dimethyl-formamide;

upstream raw materials:

Toluene-4-sulfonic acid (S)-2-benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

(2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol

(1S)-2-(benzyloxy)-1-[(4S)-2,2-dimethyl-1,3-dioxolane-4-yl]-ethan-1-ol

methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Downstream raw materials:

(6S,7R)-7-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-1,4-dimethyl-[1,4]diazepan-2-one

(6S,7R)-7-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-[1,4]diazepan-2-one

Toluene-4-sulfonic acid (2R,3R)-3-azido-4-benzyloxy-2-hydroxy-butyl ester

[((2S,3R)-3-Azido-4-benzyloxy-2-hydroxy-butyl)-methyl-amino]-acetic acid